Potassium Carbonate → (4R,5R)-4-(5-ethynyl-2-fluoropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

HRID 2362365Notes

Reaction equation

HRID 2362365 reaction equation
[F:1][C:2]1[C:7]([C@@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[O:11][C:10](=[O:20])[NH:9]2)=[CH:6][C:5]([C:21]#[C:22][Si](C)(C)C)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:21]([C:5]1[CH:6]=[C:7]([C@@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[O:11][C:10](=[O:20])[NH:9]2)[C:2]([F:1])=[N:3][CH:4]=1)#[CH:22]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69084079(4R,5R)-4-(2-fluoro-5-((trimethylsilyl)ethynyl)pyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one

Product 1

HCID 86673416(4R,5R)-4-(5-ethynyl-2-fluoropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-oneYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 25 mL round bottom flask was added (4R,5R)-4-(2-fluoro-5-((trimethylsilyl)ethynyl)pyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one (77 mg, 0.207 mmol) in MeOH (4 mL). The solution was stirred and potassium carbonate (28.6 mg, 0.207 mmol) was added in one portion and the reaction was allowed to stir for 30 min. The reaction was complete by TLC and LC/MS. The reaction solvent was then evaporated in vacuo and the crude solid was dissolved in dichloromethane and washed with saturated ammonium chloride. The organic layer was separated, dried over sodium sulfate, and evaporated in vacuo to afford (4R,5R)-4-(5-ethynyl-2-fluoropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one (60 mg, 0.180 mmol, 87% yield) as an off white solid. This material was used as is without purification. 1H-NMR (CDCl3, 400 MHz) δ 8.39 (s, 1H), 8.07 (dd, J=8.0, 2.0, 1H), 7.47-7.42 (m, 1H), 7.19-7.12 (m, 3H), 5.86 (brs, 1H), 5.37 (d, J=4.0, 1H), 5.02 (s, J=4.0, 1H), 3.31 (s, 1H). LC/Mass spec. (Analytical HPLC method 2): RT=1.82 min. Mass=301.19 (MH)+.

Workup

  1. stirringto stir for 30 min
  2. customThe reaction solvent was then evaporated in vacuo
  3. dissolutionthe crude solid was dissolved in dichloromethane
  4. washwashed with saturated ammonium chloride
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-265b2643d5f44beb9c56fddecb760395
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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